Page last updated: 2024-11-04

hexobarbital

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Hexobarbital: A barbiturate that is effective as a hypnotic and sedative. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

hexobarbital : A member of the class of barbiturates taht is barbituric acid substituted at N-1 by methyl and at C-5 by methyl and cyclohex-1-enyl groups. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID3608
CHEMBL ID7728
CHEBI ID5706
SCHEMBL ID29821
MeSH IDM0010321

Synonyms (97)

Synonym
(+/-)-hexobarbital
smr000473348
5-cyclohex-1-en-1-yl-1,5-dimethylpyrimidine-2,4,6(1h,3h,5h)-trione
MLS001143909
AC-16076
barbituric acid, 5-(1-cyclohexen-1-yl)-1,5-dimethyl-
2,4,6(1h,3h,5h)-pyrimidinetrione, 5-(1-cyclohexen-1-yl)-1,5-dimethyl-
5-cyclohex-1-en-1-yl-2-hydroxy-1,5-dimethylpyrimidine-4,6(1h,5h)-dione
5-(1-cyclohexen-1-yl)-1,5-dimethylbarbituric acid
hexenal (barbiturate)
hexabarbital
hexanastab oral
n-methyl-5-cyclohexenyl-5-methylbarbituric acid
2,6(1h,3h,5h)-pyrimidinetrione, 5-(1-cyclohexen-1-yl)-1,5-dimethyl-
barbituric acid,5-dimethyl-
wln: t6vmvnv fhj d1 f1 f- al6utj
citopan
sombucaps
evipan
noctivane
nsc71929
methylhexabital
cyclopan
narcosan
sombulex
dorico
barbidorm
nsc-71929
somnalert
1,5-dimethyl-5-(1-cyclohexenyl)barbituric acid
enhexymal
citodon
cyclonal
methylhexabarbital
evipal
methexenyl
5-(.delta.-1,2-cyclohexenyl)-5-methyl-n-methyl-barbitursaeure
5-(1-cyclohexenyl-1)-1-methyl-5-methylbarbituric acid
CHEBI:5706 ,
5-(1-cyclohexen-1-yl)-1,5-dimethyl-2,4,6(1h,3h,5h)-pyrimidinetrione
5-cyclohex-1-enyl-1,5-dimethyl-pyrimidine-2,4,6-trione
5-(cyclohex-1-en-1-yl)-1,5-dimethylpyrimidine-2,4,6(1h,3h,5h)-trione
OPREA1_350917
hexobarbital (van)
hexobarbitalum [inn-latin]
ai3-61892
hexobarbitonum
5-(delta-1,2-cyclohexenyl)-5-methyl-n-methyl-barbitursaeure [german]
nsc 71929
esobarbitale [italian]
esobarbitale [dcit]
einecs 200-264-9
enhexymalum
hexobarbitone
hexobarbital
56-29-1
NCGC00159430-02
DB01355
D01071
hexobarbital (jan/inn)
NCGC00159430-03
AKOS000355976
CHEMBL7728
hexobarbital ciii
5-(cyclohexen-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione
NCGC00159430-04
esobarbitale
unii-al8z8k3p6s
hexobarbitalum
5-(delta-1,2-cyclohexenyl)-5-methyl-n-methyl-barbitursaeure
hexobarbital [usp:inn:ban:jan]
al8z8k3p6s ,
STK696034
dtxcid903122
cas-56-29-1
tox21_111661
dtxsid9023122 ,
tox21_111662
HMS2272K03
hexobarbital [mart.]
hexobarbital [vandf]
hexobarbital [who-dd]
hexobarbital [jan]
hexobarbital [ep impurity]
hexobarbital [mi]
hexobarbital [inn]
AKOS016347605
SCHEMBL29821
tox21_111661_1
5-(cyclohexen-1-yl)-1,5-dimethylbarbituric acid
5-(cyclohexen-1-yl)-1,5-dimethylbarbitursaeure
5-(cyclohex-1-en-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione
hexobarbital, united states pharmacopeia (usp) reference standard
5-cyclohexenyl-1,5-dimethylpyrimidine-2,4,6(1h,3h,5h)-trione
hexobarbital 1.0 mg/ml in methanol
Q421183
hexobarbital, 1mg/ml in methanol

Research Excerpts

Overview

Hexobarbital is a drug widely used to study the capacity of the liver to metabolize drugs.

ExcerptReferenceRelevance
"Hexobarbital is a drug widely used to study the capacity of the liver to metabolize drugs. "( Pharmacokinetics of hexobarbital in young and old rats.
Boonstra-Nieveld, IH; van Bezooijen, CF, 1989
)
2.04

Toxicity

ExcerptReferenceRelevance
" In view of the inclusion of nicotinic acid, nicotinamide, salicylic acid, and phenylbutazone in this correlation between toxicity and 7-14C-nicotinamide mobilization, it is not necessary that the formation of compounds analogous to the nicotinamide dinucleotides plays a significant role in the toxic manifestations of the nicotinamide analogs."( Drug-biomolecule interactions: drug toxicity and vitamin coenzyme depletion.
Ahmad, N; Bederka, JP; Davitiyananda, D; Moses, ML, 1975
)
0.25
"The hepatotoxicity of acetaminophen (APAP) overdose depends on metabolic activation to a toxic reactive metabolite via hepatic mixed function oxidase."( Acetaminophen hepatotoxicity: is there a role for prostaglandin synthesis?
Ben-Zvi, Z; Danon, A; Katz, S; Weissman-Teitellman, B, 1990
)
0.28
"Fenitrothion of oral subtoxic dose (100 mg/kg; 4 hr pretreatment) decreased acute oral LD50 of BPMC from 360 to 66 mg/kg in male mice."( Potentiated toxicity of 2-sec-butylphenyl methylcarbamate (BPMC) by O,O-dimethyl O-(3-methyl-4-nitrophenyl)phosphorothioate (fenitrothion) in mice; relationship between acute toxicity and metabolism of BPMC.
Miyaoka, T; Shirasu, Y; Takahashi, H; Tsuda, S, 1984
)
0.27
" The acute oral LD50 of naphthalene was 533 and 710 mg/kg in male and female mice, respectively."( Naphthalene toxicity in CD-1 mice: general toxicology and immunotoxicology.
Anderson, AC; Barnes, DW; Borzelleca, JF; Condie, LW; Duke, SS; Hayes, JR; Holsapple, MP; Shopp, GM; White, KL, 1984
)
0.27
" Altogether the acute toxicity of the compounds under investigation may be regarded as weak, because LD50 values could be determined for only 10 of the orally applied 17 pyridazines."( [Pharmacological characterization of novel pyridazines. Part 1: Physicochemical parameters, acute toxicity and action on the central nervous system (author's transl)].
Bluth, R, 1981
)
0.26
"Twenty-four hour LD50 values of secobarbital, pentobarbital, phenobarbital, in male Swiss-Webster mice weighing approximately 30 g each."( Twenty-four hour toxicity rhythms of sedative-hypnotic drugs in mice.
Ross, FH; Sermons, AL; Walker, CA, 1980
)
0.26

Pharmacokinetics

Hexobarbital and heptabarbital were chosen for this purpose as model substrates because of their structural, pharmacokinetic as well as metabolic similarity. The influence of long-term administration of dexamethasone on pharmacodynamic activity and biotransformation of s was investigated.

ExcerptReferenceRelevance
"A few conclusive experimental models (barbiturate sleep, tetrabenazine reversion, maximum electroshock) were chosen to collect comprehensive data on the pharmacodynamic characteristics of amitriptylinoxide."( Special experiments on central nervous effects of amitriptylinoxide considering pharmacokinetic aspects.
Wenzl, H, 1978
)
0.26
" It could be seen that the pharmacokinetic model changes from an open one-compartment model to an open two-compartment model in dependence of the time of application."( [Circadian-induced change in the pharmacokinetic pattern exemplified on hexobarbital/Retrospective analysis of experimental data (author's transl)].
Altmayer, P; Lücker, PW; Rindt, W, 1979
)
0.49
" Serum concentrations of hexobarbital were determined by HPLC procedure and the resulting pharmacokinetic parameters in a rotating iterative program."( [Circadian fluctuations of pharmacokinetic parameters after oral administration of hexobarbital (author's transl)].
Altmayer, P; Groterath, E; Lücker, PW; Mayer, D; Rindt, W; von Mayersbach, H; Wetzelsberger, K, 1979
)
0.79
" The average elimination half-life of hexobarbital had decreased from 624 to 262 min and that of tolbutamide from 292 to 160 min following rifampicin treatment."( Stimulation of drug metabolism by rifampicin in patients with cirrhosis or cholestasis measured by increased hexobarbital and tolbutamide clearance.
Breimer, DD; Richter, E; Zilly, W, 1977
)
0.74
" The elimination half-life of hexobarbital was 490 +/- 186 min in the hepatitis patients and 261 +/- 69 min in the control group."( Pharmacokinetics of hexobarbital in acute hepatitis and after apparent recovery.
Breimer, DD; Richter, E; Zilly, W, 1975
)
0.87
" Pharmacodynamic activity of salicylamide, morphine and hexobarbital were investigated."( Influence of disorders of adrenal function of activity and pharmacokinetics of some neurotropic drugs. I. Influence of adrenalectomy on potency and pharmacokinetics of drugs.
Cenajek, D, 1975
)
0.5
"The influence of long-term administration of dexamethasone on pharmacodynamic activity and biotransformation of salicylamide and hexobarbital, including their absorption, distribution and excretion, were studied."( Influence of adrenal dysfunction on activity and pharmacokinetics of some neutropic drugs. II. Influence of chronic premedication with dexamethasone on pharmacodynamic activity and pharmacokinetics of drugs.
Cenajek, D; Szczawinńska, K, 1975
)
0.46
" The average elimination half-life of hexobarbital had decreased from 325 to 122 min and of tolbutamide from 418 to 183 min following rifampicin treatment."( Induction of drug metabolism in man after rifampicin treatment measured by increased hexobarbital and tolbutamide clearance.
Breimer, DD; Richter, E; Zilly, W, 1975
)
0.75
" The quantities applied in this case are so small that pharmacodynamic effects do not occur."( [Applications of positron emission tomography (PET) to the measurement of regional cerebral pharmacokinetics].
Stöcklin, G, 1992
)
0.28
" For S-hexobarbital the half-life is somewhat shorter and the volume of distribution and plasma clearance is higher than for its antipode."( Influence of age on stereoselective pharmacokinetics and metabolism of hexobarbital in the rat.
Belpaire, FM; Bogaert, MG; De Smet, F; Rosseel, MT; Vermeulen, AM, 1992
)
0.97
" The half-life of hexobarbital in 30-month-old rats (39."( Pharmacokinetics of hexobarbital in young and old rats.
Boonstra-Nieveld, IH; van Bezooijen, CF, 1989
)
0.93
" It was found that in all variants of the liver denervation there occurs an increase of the period of half-life and a decrease of clearance of the drugs."( [Pharmacokinetic characteristics of drug substance in liver denervation].
Ashirmetov, AKh; Krakovskiĭ, ME,
)
0.13
"The metabolic clearance (CL) and half-life of racemic hexobarbitone and sleeping time were studied in rats following intra-arterial (i."( Route- and dose-dependent pharmacokinetics of hexobarbitone in the rat: a re-evaluation of the use of sleeping times in metabolic studies.
Breimer, DD; Van der Graaff, M; Vermeulen, NP, 1985
)
0.27
" It was found that the half-life of all the drugs increased and plasma clearance decreased."( [Pharmacokinetic characteristics of drugs in experimental splenectomy].
Ashirmetov, AKh; Krakovskiĭ, ME,
)
0.13
" When employing HB as a model substrate for drug metabolizing enzyme activity in vivo, the determination of its pharmacokinetic parameters, particularly oral plasma clearance as a reflection of cytochrome P-450 activity, cannot be achieved by taking saliva samples only."( Pharmacokinetics of orally administered hexobarbital in plasma and saliva of healthy subjects.
Boeijinga, JK; Breimer, DD; Heij, P; van der Graaff, M; Vermeulen, NP,
)
0.4
" In both sexes, the total body clearance and volume of distribution of HB were decreased by 20% during phototherapy of the jj but not the Jj rats; terminal plasma half-life was unchanged."( Effects of phototherapy on the activity of microsomal mixed-function monooxygenases and the pharmacokinetics of [14C] hexobarbital in jaundiced and heterozygous Gunn rats.
Kapitulnik, J; Ostrow, JD; Tabata, M; Webster, CC; Zucker, GM, 1986
)
0.48
" Hexobarbital and heptabarbital were chosen for this purpose as model substrates because of their structural, pharmacokinetic as well as metabolic similarity."( Pharmacokinetics of simultaneously administered hexobarbital and heptabarbital in rats: an alternative approach to metabolic correlation studies.
Breimer, DD; Langendijk, PN; van der Graaff, M; Vermeulen, NP, 1983
)
1.43
"A physiologically based pharmacokinetic model, which is an extension of the Bischoff-Dedrick multiorgan model, was developed to described the kinetics of barbiturates (hexobarbital, phenobarbital, and thiopental) in the rat."( Comparative physiologically based pharmacokinetics of hexobarbital, phenobarbital and thiopental in the rat.
Awazu, S; Hanano, M; Igari, Y; Sugiyama, Y, 1982
)
0.71
" However, changes in pharmacokinetic parameters of elimination from the blood of the drugs based on microsomal substrates of hepatic enzymatic system are more dependent on the microwaves' impact on physiological factors modifying drug pharmacokinetics."( [The characteristics of the effect of centimeter-range microwaves on drug pharmacokinetics in the body of experimental animals].
Gorchakova, GA; Grishanova, AIu; Guliaeva, LF; Liakhovich, VV; Zolotareva, TA,
)
0.13
" pharmacokinetic data on 670 drugs representing, to our knowledge, the largest publicly available set of human clinical pharmacokinetic data."( Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
Lombardo, F; Obach, RS; Waters, NJ, 2008
)
0.35

Compound-Compound Interactions

ExcerptReferenceRelevance
"The most widely used H2-receptor antagonist, cimetidine, is known to interact with cytochrome P-450 drug-metabolizing enzymes and, therefore, interacts with other drugs which may be administered concurrently."( Comparative effects of H2-receptor antagonists on drug interaction in rats.
Cocchetto, DM; Duggan, DE; Lin, JH; Yeh, KC,
)
0.13
" Consequently, the occurrence of drug-drug interactions of chlorphenethazine and chlorpromazine cannot be excluded in the framework of combined therapy."( [Metabolic drug-drug interactions of chlorphenethiazine and chlorpromazine].
Bina, B; Borchert, HH; Pfeifer, S, 1984
)
0.27

Bioavailability

The study looked at metabolism of four analogous barbiturates. In four subjects who received intravenous and oral hexobarbital, systemic clearance was 36% lower while bioavailability was 10% greater during CBD.

ExcerptReferenceRelevance
" The maximum rate of absorption was registered with 3 and 5 per cent concentrations, while 1 and 10 per cent solutions are absorbed at a slower rate."( [Glucose transport across the mucosa of the small intestine].
Kosarev, AV,
)
0.13
" Profiles of metabolism of four analogous barbiturates (N-methylcyclobarbital, hexobarbital, cyclobarbital and norhexobarbital), which have a cyclohexene ring on the 5-carbon, reveal the contribution of alkyl substituents in the barbiturate ring on the bioavailability and metabolism of these compounds."( Biotransformation of N-methylcyclobarbital in vivo in rabbit and rat.
Miyano, K; Shimodouzono, Y; Toki, S, 1985
)
0.5
"), total pepsin output, and is well absorbed from the gastrointestinal tract."( Pharmacological profile of etintidine, a new histamine H2-receptor antagonist.
Katz, LB; Scott, CK; Shriver, DA, 1986
)
0.27
" Haem arginate administered in high doses prior to oral propranolol did not alter the bioavailability of the latter."( Barbiturate and ethanol sleeping times and pharmacokinetics of propranolol in mice after intravenous administration of haem arginate.
Tokola, O, 1987
)
0.27
" In four subjects who received intravenous and oral hexobarbital, systemic clearance was 36% lower while bioavailability was 10% greater during CBD."( Metabolic and psychophysiologic studies of cannabidiol-hexobarbital interaction.
Bachman, J; Benowitz, NL; Herning, RI; Jones, RT; Nguyen, TL, 1980
)
0.76
" Also there is no evidence as yet, that patients with liver disease and without a collateral portal circulation do have an increased bioavailability of oral high clearance drugs."( [Drug metabolism in patients with liver disease (author's transl)].
Epping, J; Fuchshofen-Röckel, M; Heusler, H; Richter, E; Zilly, W, 1980
)
0.26
"The quantitative structure-bioavailability relationship of 232 structurally diverse drugs was studied to evaluate the feasibility of constructing a predictive model for the human oral bioavailability of prospective new medicinal agents."( QSAR model for drug human oral bioavailability.
Topliss, JG; Yoshida, F, 2000
)
0.31
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

Caffeine caused a shift in the dose-response curve for hexobarbital but no changes in hexobarBital distribution and elimination. 1,5-dimethylbarbituric acid was excreted into the urine and the cyclohexenone-glutathione adduct into the bile of rats dosed with hexobar Bital.

ExcerptRelevanceReference
" We conclude this to be the result of limited dosage and maintenance of adequate ventilation and oxygenation."( Topical application of epinephrine during bronchoscopy in barbiturate-halothane-anaesthesia and its influence on cardiac action.
Abel, H; Mall, W,
)
0.13
" The magnitude of the response was greater in tolerant animals, but no parallel shift in the dose-response curve was seen."( The effects of atropine on the tolerance and the convulsions seen after withdrawal from forced barbital drinking in the rat.
Wahlström, G, 1978
)
0.26
" Caffeine caused a shift in the dose-response curve for hexobarbital but no changes in hexobarbital distribution and elimination."( Hexobarbital blood levels and effects on EEG in the presence and absence of caffeine.
Atkinson, J; Milon, H, 1979
)
1.95
" This effect may be easily suspended by interrupting drug administration or inducing microsomal enzymes with a single dosage of testosterone."( Short-term and prolonged treatment with oral contraceptives and liver function.
Kulcsár, A; Kulcsár-Gergely, J, 1977
)
0.26
"Studies of hexobarbital sleeping time in rats showed that only a very high dosage of ethyl(Z)-(3-ethyl-4-oxo-5-piperidino-thiazolidin-2-ylidene)-acetate (piprozoline, Gö 919, Problin) (500 mg/kg) produced a weak interaction with the metabolism of hexobarbital; no signs of any induction of the oxidative enzyme system were observed until 4 days after pre-treatment with 3 X 250 mg/kg."( [Studies on the influence of piprozoline on the microsomal enzyme system of the rat liver (author's transl)].
Friedrich, G; Vollmer, KO, 1977
)
0.65
" A dose-response increase in sodium hexobarbital induced narcosis was produced by Dopram(R)."( Evaluation of Dopram(R) and its effects on hexobarbital narcosis.
Flint, BA; Ho, IK, 1978
)
0.8
"Studies were conducted in an effort to determine if a circadian rhythm in response of mice to hexobarbital could be evaluated employing dose-response curves."( Circadian rhythm in hexobarbital sleep time: a dose-response evaluation in the mouse.
Holcslaw, TL, 1978
)
0.8
" In the dose-response study pilocarpine was given 1 h prior to the hexobarbital threshold determination."( The interaction between pilocarpine and hexobarbital in male rats.
Wahlström, G, 1976
)
0.76
"Mice were given several atropine injections at a high dosage level."( Sensitivity changes to morphine and other drugs induced by cholinergic blockade.
Contreras, E; Quijada, L; Tamayo, L, 1975
)
0.25
" Both At and Sc in a wide range of dosage protect against the tonic phase of convulsions produced by electroshock."( Central action of drugs acting on the cholinergic muscarinic receptor. III. Influence of atropine and scopolamine injected intraventricularly on behavior and levels of biogenic amines in the rat brain.
Kleinrok, Z; Poddubiuk, Z; Zebrowska-Lupina, I, 1975
)
0.25
" As to the dose-response study, the prolongation of the hexobarbital-induced sleeping time in young male is statistically significant when fed with 30 cal% in RSO for 3 days, while it is not more statistically significant in mice fed 15 cal% in RSO."( Effect of dietary rapeseed oil on hepatic hexobarbital metabolism in mice.
del Carmine, R; Gatti, GL; Michalek, H, 1975
)
0.76
" The whole-body concentrations of hexobarbital (100 mg/kg dose) in mice 30 min after dosing were 14."( Inhibition and induction of drug metabolism by psoralens: alterations in duration of sleep induced by hexobarbital and in clearance of caffeine and hexobarbital in mice.
Apseloff, G; Gerber, N; Hilliard, JB; Mays, DC, 1991
)
0.78
" A single oral 24-hr pretreatment with CVP (15 mg/kg) increased the oral LD50 of its next dosage to threefold."( Metabolic induction of the hepatic cytochrome P450 system by chlorfenvinphos in rats.
Ikeda, T; Shirasu, Y; Tsuda, S, 1991
)
0.28
" Stereoselective differences between the enantiomers of 2a and 2b were observed only when a dose of 200 mg/kg was applied, whereas the higher activity of the (S)-enantiomers of 2c, 1b + c was obtained already with a lower dosage range."( [Stereoselective differences of central nervous system-depressive action of a homologous series of 3-alkyl-thalidomide analysis].
Büch, HP; Knabe, J; Omlor, G, 1990
)
0.28
" This has been applied to the analysis of some of these drugs in plasma taken from patients after therapeutic dosage and over-dosage."( A rapid micro-method for the screening and measurement of barbiturates and related compounds in plasma by gas-liquid chromatography.
Flanagan, RJ; Withers, G, 1972
)
0.25
" Other organ weights were unaffected at any dosage level."( Naphthalene toxicity in CD-1 mice: general toxicology and immunotoxicology.
Anderson, AC; Barnes, DW; Borzelleca, JF; Condie, LW; Duke, SS; Hayes, JR; Holsapple, MP; Shopp, GM; White, KL, 1984
)
0.27
"Chlordiazepoxide HCl, a widely used tranquilizer, was evaluated for pre- and postnatal effects in rats by dosing orally on days 1--21 of gestation."( Effects of chlordiazepoxide on the pre- and postnatal development of rats.
Buttar, HS, 1980
)
0.26
" Similar effects were observed with chronic dosing of cimetidine."( Cimetidine: a specific inhibitor of hepatic aryl hydrocarbon hydroxylase (AHH) in the rat.
Drew, R; Grygiel, JJ; Rowell, J, 1981
)
0.26
"Hexobarbital sleeping time was prolonged and ethylmorphine N-demethylation was inhibited after a single dosage or seven administration of 6-SAI to old rats."( Drug metabolism in rats with arthritis induced by 6-sulfanilamidoindazole (6-SAI).
Hirschelmann, R; Müller, D, 1981
)
1.71
" Dose-response curve for flumazenil (2."( Interaction between flumazenil and the anesthetic effects of hexobarbital in the rat.
Korkmaz, S; Ljungblad, E; Wahlström, G, 1995
)
0.53
" The effects of the steroid solvents albumin and beta-cyclodextrin were assessed by dose-response curves."( Pregnenolone sulphate and pregnenolone do not interact with 5 beta-pregnanolone- and hexobarbitone-induced anaesthesia in the rat.
Bäckström, T; Wahlström, G; Wang, MD, 1997
)
0.3
" A dose-response relationship with regard to lorazepam (0."( Development of physical dependence to lorazepam in rats: the effects of repeated short treatments, dose and age.
Carlsson, S; Korkmaz, S; Wahlström, G, 1998
)
0.3
" 1,5-dimethylbarbituric acid was excreted into the urine and the cyclohexenone-glutathione adduct into the bile of rats dosed with hexobarbital."( [New aspects of hexobarbital metabolism: stereoselective metabolism, new metabolic pathway via GSH conjugation, and 3-hydroxyhexobarbital dehydrogenases].
Takenoshita, R; Toki, S, 2004
)
0.87
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
barbituratesMembers of the class of pyrimidones consisting of pyrimidine-2,4,6(1H,3H,5H)-trione (barbituric acid) and its derivatives. Largest group of the synthetic sedative/hypnotics, sharing a characteristic six-membered ring structure.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (13)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency0.07940.003245.467312,589.2998AID2517
AR proteinHomo sapiens (human)Potency13.44810.000221.22318,912.5098AID743035
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency33.49150.001022.650876.6163AID1224838
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency4.21630.001530.607315,848.9004AID1224841
activating transcription factor 6Homo sapiens (human)Potency0.53540.143427.612159.8106AID1159516
chromobox protein homolog 1Homo sapiens (human)Potency79.43280.006026.168889.1251AID540317
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency12.99530.00419.984825.9290AID504444
importin subunit beta-1 isoform 1Homo sapiens (human)Potency0.46115.804836.130665.1308AID540253
snurportin-1Homo sapiens (human)Potency0.46115.804836.130665.1308AID540253
GTP-binding nuclear protein Ran isoform 1Homo sapiens (human)Potency0.46115.804816.996225.9290AID540253
gemininHomo sapiens (human)Potency0.58050.004611.374133.4983AID624297
peripheral myelin protein 22Rattus norvegicus (Norway rat)Potency20.26790.005612.367736.1254AID624032
Spike glycoproteinSevere acute respiratory syndrome-related coronavirusPotency0.70790.009610.525035.4813AID1479145
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
virion membraneSpike glycoproteinSevere acute respiratory syndrome-related coronavirus
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (70)

Assay IDTitleYearJournalArticle
AID540213Half life in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID38915Negative log of molar concentration (-log ED50) required to reduce cell division by 50% in Arbacia egg; ND = No Data1983Journal of medicinal chemistry, Jul, Volume: 26, Issue:7
A simplified high-pressure liquid chromatography method for determining lipophilicity for structure-activity relationships.
AID1130940Retention index of the compound by HPLC method1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Correlation of biological activity and high-pressure liquid chromatographic retention index for a series of propranolol, barbiturate, and anthranilic acid analogues.
AID588212Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1149367Acute toxicity in po dosed mouse1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Synthesis and antiinflammatory and hypnotic activity of 5-alkoxy-3-(N-substituted carbamoyl)-1-phenylpyrazoles.
AID237685Lipophilicity determined as logarithm of the partition coefficient in the alkane/water system2005Journal of medicinal chemistry, May-05, Volume: 48, Issue:9
Calculating virtual log P in the alkane/water system (log P(N)(alk)) and its derived parameters deltalog P(N)(oct-alk) and log D(pH)(alk).
AID588213Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in non-rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID425652Total body clearance in human2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Physicochemical determinants of human renal clearance.
AID540209Volume of distribution at steady state in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID29359Ionization constant (pKa)2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID588211Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in humans2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID27167Delta logD (logD6.5 - logD7.4)2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID540210Clearance in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID29811Oral bioavailability in human2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID346025Binding affinity to beta cyclodextrin2009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
Convenient QSAR model for predicting the complexation of structurally diverse compounds with beta-cyclodextrins.
AID25090A pKa value is evaluated1983Journal of medicinal chemistry, Jul, Volume: 26, Issue:7
A simplified high-pressure liquid chromatography method for determining lipophilicity for structure-activity relationships.
AID1130943Octanol-water partition coefficient, log P of nonionized form of compound1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Correlation of biological activity and high-pressure liquid chromatographic retention index for a series of propranolol, barbiturate, and anthranilic acid analogues.
AID1130944Hypnotic activity in rabbit1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Correlation of biological activity and high-pressure liquid chromatographic retention index for a series of propranolol, barbiturate, and anthranilic acid analogues.
AID28681Partition coefficient (logD6.5)2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID603953In-vivo plasma to lung partition coefficients of the compound, logP(lung) in rat2008European journal of medicinal chemistry, Mar, Volume: 43, Issue:3
Air to lung partition coefficients for volatile organic compounds and blood to lung partition coefficients for volatile organic compounds and drugs.
AID169098Negative log of molar concentration (-log C) required to produce 50% inhibition of oxygen (oxygen uptake) on rat brain respiration in vitro; ND = No Data1983Journal of medicinal chemistry, Jul, Volume: 26, Issue:7
A simplified high-pressure liquid chromatography method for determining lipophilicity for structure-activity relationships.
AID540211Fraction unbound in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1149366Hypnotic activity in ip dosed ddN mouse assessed as loss of righting reflex administered as gum arabic suspension measured within 60 mins1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Synthesis and antiinflammatory and hypnotic activity of 5-alkoxy-3-(N-substituted carbamoyl)-1-phenylpyrazoles.
AID425653Renal clearance in human2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Physicochemical determinants of human renal clearance.
AID540212Mean residence time in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID167610Negative log of minimum effective dose (moles per kilogram) in rabbits (hypnotic)1983Journal of medicinal chemistry, Jul, Volume: 26, Issue:7
A simplified high-pressure liquid chromatography method for determining lipophilicity for structure-activity relationships.
AID24211Compound is evaluated for ionization constant log k1983Journal of medicinal chemistry, Jul, Volume: 26, Issue:7
A simplified high-pressure liquid chromatography method for determining lipophilicity for structure-activity relationships.
AID1347097qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Saos-2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347093qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347108qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh41 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347105qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for MG 63 (6-TG R) cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347107qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh30 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347089qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for TC32 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347101qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID1347100qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347104qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347425Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347407qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Pharmaceutical Collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1347102qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh18 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347094qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347099qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347090qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for DAOY cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347098qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347091qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347095qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347103qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347092qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347106qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for control Hh wild type fibroblast cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347096qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for U-2 OS cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347424RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (2,188)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901961 (89.63)18.7374
1990's124 (5.67)18.2507
2000's60 (2.74)29.6817
2010's31 (1.42)24.3611
2020's12 (0.55)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 37.08

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index37.08 (24.57)
Research Supply Index7.82 (2.92)
Research Growth Index4.14 (4.65)
Search Engine Demand Index61.55 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (37.08)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials11 (0.44%)5.53%
Reviews41 (1.65%)6.00%
Case Studies11 (0.44%)4.05%
Observational0 (0.00%)0.25%
Other2,427 (97.47%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]